As Fall is just about here, it’s time to address a permanently popular look and why it’s so rarely done right. Every September, women get excited about pairing boots with skirts and dresses, and although so many love this look, few know how to wear it correctly. Let me help you fix this-

The reason boots+skirt often looks wrong is because you’re not investing in the best boots like Stuart Weitzman (pictured above), instead short cutting with a cheap option like Steve Madden (pictured below). Cheap boots use bad leather and crap hardware which combines for a sloppy presentation. Additionally, many of you are choosing boots that are too chunky in the sole, the silhouette, and the hardware, like the popular FRYE Harness model, which works with jeans but little else.

Here are my top choices for boots that will pull off this look: FRYE Anna Inside Zip, FRYE Melissa Scrunch, Loeffler Randall Matilde Tall, Stuart Weitzman Gentry, & Rachel Comey Carrier.

Images via Stuart Weitzman & Steve Madden.